Oregon Trail was a game I originally played on the Apple IIe a long time ago. The concept was simple: put your family on a caravan and try to get to Oregon. You could die in all sorts of horrible ways, from raids to starvation to dysentery. Combine traveling in a hostile environment, plus trading, plus bands of post-apocalyptic renegades, and you have the Flash-based game Caravaneer.
Caravaneer is free to play and is played via your Web browser. You’ll need Flash to play, but that’s about it. You start out with an inheritance from an uncle (who was killed by robbers, nice warning) and a mule. The initial “trade route” is between three towns: buy leather at your home town, take it to town B where you sell the leather for shoes. Take the shoes to town C, where you sell the shoes for clothes and medicine, which you then sell back in your home town. Repeat until you have enough money to buy a henchman, a cart for your donkey, and upgraded water containers. I currently have three donkeys with carts and two henchmen, all packing rifles and body armor.

Unlike most Flash games, Caravaneer allows you to save your game — which I highly recommend doing, especially since there is no way to escape once you are beset by robbers. You must kill them all or be killed. Hell yeah, Mad Max Thunderdome style, bitches. I thought I was hot shit until I got jumped by ten robbers with rifles. We barely made it out alive, but then I died on the outskirts of town due to my injuries. I hadn’t saved beforehand, and I lost a horse, cart, and bunch of weapons. Damn.

The biggest complaint I have about the game is that the map isn’t dynamic, and it’s easy to get lost from town to town, especially on long voyages. You can measure the angle from your current location to your destination in degrees, and then you set your path accordingly. However, if you’re off by a few degrees and are going a long way, you can get lost in the desert. The burn food, water, and animal chow (forage) as you travel, so you can die out in the desert without encountering a single hostile.

Give Caravaneer a try. You’ll die quickly the first few times until you get the hang of it, but it’s a great way to pass the time. Big thanks to Bond for suggesting this to me. It’s been a lot of fun.

Hrm, I haven’t gotten that far in the game. I’ve been fixated on selling shoes from the newbie towns to Verdammter Platz. I believe I have the top grade body armor, but have been unwilling to fit my group with anything softer-hitting than the 7.62×51 NATO (.308) Mini-14.

I have considered going to all horses and/or ATVs and raiding caravans and the Desert Squad. Maybe you can try taking on the “good guys.”